Star-Shaped ESIPT-Active Mechanoresponsive Luminescent AIEgen and Its On–Off–On Emissive Response to Cu2+/S2

Design and development of multifunctional materials have drawn incredible attraction in recent years. Herein, we report the design and construction of versatile star-shaped intramolecular charge transfer (ICT)-coupled excited-state intramolecular proton transfer (ESIPT)-active mechanoresponsive and...

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Veröffentlicht in:ACS omega 2019-07, Vol.4 (7), p.12459-12469
Hauptverfasser: Tharmalingam, Balamurugan, Mathivanan, Moorthy, Dhamodiran, Ganesh, Saravana Mani, Kailasam, Paranjothy, Manikandan, Murugesapandian, Balasubramanian
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Sprache:eng
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Zusammenfassung:Design and development of multifunctional materials have drawn incredible attraction in recent years. Herein, we report the design and construction of versatile star-shaped intramolecular charge transfer (ICT)-coupled excited-state intramolecular proton transfer (ESIPT)-active mechanoresponsive and aggregation-induced emissive (AIE) luminogen triaminoguanidine-diethylaminophenol (LH3 ) conjugate from simple precursors triaminoguanidine hydrochloride and 4-(N,N-diethylamino)­salicylaldehyde. Solvent-dependent dual emission in nonpolar to polar protic solvents implies the presence of ICT-coupled ESIPT features in the excited state. Aggregation-enhanced emissive feature of LH3 was established in the CH3CN/water mixture. Furthermore, this compound exhibits mechanochromic fluorescence behavior upon external grinding. Fluorescence microscopy images of pristine, crystal, and crushed crystals confirm the naked-eye mechanoresponsive characteristics of LH3 . In addition, LH3 selectively sensed a Cu2+ ion through a colorimetric and fluorescence “turn-off” route, and subsequently, the LH3 -Cu2+ ensemble could act as a selective and sensitive sensor for S2– in a “turn-on” fluorescence manner via a metal displacement approach. Reversible “turn-off–turn-on” features of LH3 with Cu2+/S2– ions were efficiently demonstrated to construct the IMPLICATION logic gate function. The Cu2+/S2–-responsive sensing behavior of LH3 was established in the paper strip experiment also, which can easily be characterized by the naked eye under daylight as well as a UV lamp (λ = 365 nm).
ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.9b00845